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E 200

E 200 or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative.
E 200 is a colourless solid that is slightly soluble in water and sublimes readily.
E 200 has the chemical formula CH3(CH)4CO2H and the structure H3C−CH=CH−CH=CH−C(=O)OH.

CAS Number: 110-44-1
EC Number: 203-768-7
IUPAC Name: (2E,4E)-Hexa-2,4-dienoic acid
Chemical Formula: C6H8O2

Other names: (E,E)-2,4-Hexadienoic acid, 1,3-Pentadiene-1-carboxylic acid, (E,E)-, 2,4-Hexadienoic acid, 2,4-Hexadienoic acid, (2E,4E)-, 2,4-Hexadienoic acid, (E,E)-, 2-Propenylacrylic acid, 2E,4E-Hexadienoic acid, Acetic acid, (2-butenylidene)-, Acetic acid, crotylidene-, alpha-trans-gamma-trans-Sorbic acid, Hexa-2,4-dienoic acid, Hexa-2,4-dienoic acid, hexa-2,4-dienoic acid, Hexa-2,4-dienoic acid (Sorbic acid), Hexadienoic acid, Kyselina sorbova, Panosorb, Sorbic acid, sorbic acid, Sorbistat, trans,trans-Sorbic acid, trans-trans-2,4-Hexadienoic acid, 2,4-hexadién sav (Szorbinsav) (hu), Acid hexa-2,4-dienoic (Acid sorbic) (ro), Acide hexa-2,4-diénoïque (acide sorbique) (fr), Acido esa-2,4-dienoico (Acido sorbico) (it), Aċidu eża-2,4-dienoiku (Aċidu sorbiku) (mt), Heksa-2,4-dieenhape (sorbiinhape) (et), Heksa-2,4-dieenihappo (sorbiinihappo) (fi), Heksa-2,4-dieno rūgštis (sorbo rūgštis) (lt), Heksa-2,4-dienoična kiselina (sorbinska kiselina) (hr), Heksa-2,4-diēnskābe (sorbīnskābe) (lv), Hexa-2,4-dieenzuur (sorbinezuur) (nl), Hexa-2,4-dienoic acid (Sorbic acid) (no), hexa-2,4-dienová kyselina (kyselina sorbová) (cs), Hexa-2,4-diensyra (Sorbinsyra) (sv), hexa-2,4-diensyre (sorbinsyre) (da), Hexa-2,4-diensäure (Sorbinsäure) (de), Kwas (2E,4E)-heksa-2,4-dienowy (kwas sorbinowy) (pl), kyselina hexa-2,4-diénová (kyselina sorbová) (sk), Ácido hexa-2,4-dienoico (ácido sórbico) (es), Ácido hexa-2,4-dienóico (ácido sórbico) (pt), Εξα-2,4-διενοϊκό οξύ (σορβικό οξύ) (el), Хекса-2,4-диенова киселина (сорбинова киселина) (bg), 2,4-Hexadienoic acid, (2E,4E)-, (2E,4E)-hexa-2,4-dienoic acid, (E,E)-2,4-Hexadienoic acid, (E,E)-2,4-Hexadienoic acid., (E,E)-hexa-2,4-dienoic acid, 2,4 Hexadienoic acid, 2,4-HEXADIENOIC ACID, 2,4-Hexadienoic acid, 2,4-Hexadienoic acid, (2E,4E)-, 2E,4E)-hexa-2,4-dienoic acid, acid hexa-2,4-dienoic, Acido Sorbico E200, Hexa-2,4-dienoic acid, hexa-2,4-dienoic acid, Hexa-2,4-dienoic acid, SORBIC ACID, Sorbic Acid, Sorbic acid, sorbic acid, Sorbic Acid, Szorbinsav, 110-44-1, 91751-55-2, 91751-55-2, 1197240-56-4, 1197240-56-4, sorbic acid, 110-44-1, 2,4-Hexadienoic acid, (2E,4E)-hexa-2,4-dienoic acid, 2E,4E-Hexadienoic acid, Panosorb, Sorbistat, 2-Propenylacrylic acid, Hexadienoic acid, trans,trans-Sorbic acid, Hexa-2,4-dienoic acid, (E,E)-2,4-Hexadienoic acid, 2,4-Hexadienoic acid, (2E,4E)-, 2,4-Hexadienoic acid, (E,E)-, alpha-trans-gamma-trans-Sorbic acid, Preservastat, (E,E)-Sorbic acid, trans,trans-2,4-Hexadienoic acid, Crotylidene acetic acid, Kyselina sorbova, Acetic acid, crotylidene-, (2E,4E)-2,4-Hexadienoic acid, (E,E)-1,3-pentadiene-1-carboxylic acid, 22500-92-1, Acetic acid, (2-butenylidene)-, trans-trans-2,4-Hexadienoic acid, Hexadienoic acid, (E,E), (2-Butenylidene)acetic acid, C6:2n-2,4, Sorbic acid (NF), Sorbic acid [NF], 1,3-Pentadiene-1-carboxylic acid, 1,3-Pentadiene-1-carboxylic acid, (E,E)-, E 200, Kyselina 1,3-pentadien-1-karboxylova, (2-butenylidene) acetic acid, FEMA NO. 3921, CHEBI:38358, INS-200, X045WJ989B, NSC-35405, NSC-49103, NSC-50268, 5309-56-8, NCGC00091737-01, .alpha.-trans-.gamma.-trans-Sorbic acid, DSSTox_CID_1277, 2,4-Hexadienoic acid, (2E,4E)-, homopolymer, DSSTox_RID_76053, DSSTox_GSID_21277, Hexadienic acid, Caswell No. 801, Sorbic Acid [USAN], Acidum sorbicum, Kyselina sorbova [Czech], 34344-66-6, CAS-110-44-1, Sorbic acid solution, CCRIS 5748, HSDB 590, (2E)-2,4-Hexadienoic acid, EINECS 203-768-7, Sorbic acid, (E,E)-, EPA Pesticide Chemical Code 075901, Sorbinsaeure, Sorbinsaure, sorbic-acid, NSC49103, UNII-X045WJ989B, AI3-14851, E-sorbic acid, trans,trans-SA, Kyselina 1,3-pentadien-1-karboxylova [Czech], (E,E)-Sorbic acid; Sorbic acid, Sorbic Acid FCC, Hexa-2,4-dienoic acid, (E,E)-, 2,4-Hexadiensaeure, MFCD00002703, Crotylidene-Acetic acid, starbld0040592, SORBIC ACID [II], SORBIC ACID [MI], SORBIC ACID [FCC], EC 203-768-7, SCHEMBL1647, SORBIC ACID [HSDB], SORBIC ACID [INCI], SORBIC ACID [VANDF], SORBIC ACID [MART.], Sorbic acid, >=99.0%, MLS002152937, (2-butenylidene)-Acetic acid, SORBIC ACID [USP-RS], SORBIC ACID [WHO-DD], (E,E)-SA, CHEMBL250212, (e,e)-hexa-2,4-dienoic acid, DTXSID3021277, Sorbic acid, analytical standard, CHEBI:35962, FEMA 3921, HMS3039E13, SORBIC ACID [EP MONOGRAPH], Sorbic acid, potassium salt (van), HY-N0626, STR09707, ZINC1558385, Tox21_111164, Tox21_201719, Tox21_300182, 2,4-SA, LMFA01030100, s4983, (2E,4E)-2,4-Hexadienoic acid #, 2, 4-Hexadienoic acid potassium salt, AKOS000119456, CCG-266056, 2,4-Hexadienoic acid, (trans,trans)-, 2,4-Hexadienoic acid, >=99%, FCC, NCGC00091737-02, NCGC00091737-03, NCGC00091737-05, NCGC00253957-01, NCGC00259268-01, E200, SMR001224532, Sorbic acid, tested according to Ph.Eur., Sorbic acid, SAJ first grade, >=98.5%, CS-0009618, S0053, Sorbic acid 1000 microg/mL in Acetonitrile, Sorbic acid, Vetec(TM) reagent grade, 98%, (E,E)-2,4-HEXADIENOIC ACID [FHFI], EN300-17945, Sorbic acid, for synthesis, 99.0-101.0%, alpha-trans-Laquo gammaRaquo -trans-sorbic acid, D05892, E80726, EN300-332923, Hexadienoic acid1,3-pentadiene-1-carboxylic acid, A829400, AN-651/40229308, Q407131, J-002425, J-524281, Z57127888, F8886-8255, Sorbic acid, European Pharmacopoeia (EP) Reference Standard, Sorbic acid, United States Pharmacopeia (USP) Reference Standard, Sorbic acid, Pharmaceutical Secondary Standard; Certified Reference Material, (2E,4E)-2,4-Hexadienoic acid [ACD/IUPAC Name], (2E,4E)-2,4-Hexadiensäure [German] [ACD/IUPAC Name], (2E,4E)hexa-2,4-dienoic acid, (2E,4E)-hexa-2,4-dienoic acid, (E,E)-1,3-Pentadiene-1-carboxylic acid, (E,E)-2,4-Hexadienoic acid, 1098547 [Beilstein], 110-44-1 [RN], 2,4-Hexadienoic acid, (2E,4E)- [ACD/Index Name], 2,4-Hexadienoic acid, (E,E)-, 2E,4E-Hexadienoic acid, Acide (2E,4E)-2,4-hexadiénoïque [French] [ACD/IUPAC Name], Acidum sorbicum, C6:2n-2,4, Sorbic acid [Wiki], trans,trans-2,4-hexadienoic acid, trans,trans-sorbic acid, trans-trans-2,4-Hexadienoic acid, WG2100000, X045WJ989B, α-trans-γ-trans-sorbic acid, "2,4-HEXADIENOIC ACID", "HEXA-2,4-DIENOIC ACID", (2-butenylidene)-Acetic acid, (2-Butenylidene)acetic acid, (2e,4e);-hexa-2,4-dienoic acid, (2E,4E)-Hexa-2,4-dienoate, (4E)-Hexa-2,4-dienoic acid, (E,E)-hexa-2,4-dienoic acid, (E,E)-SORBIC ACID, 1,3-Pentadiene-1-carboxylic acid, 1,3-Pentadiene-1-carboxylic acid, (E,E)-, 198544-42-2 [RN], 2, 4-Hexadienoic acid, 2,4-Hexadienic acid, 2,4-Hexadienoic acid, (trans,trans)-, 2,4-HexadienoicAcid, 2,4-Hexadiensaeure, 2,4-HEXANEDIENOIC ACID, 2-Propenylacrylic acid, 91751-55-2 secondary RN [RN], Acetic acid, (2-butenylidene)-, Acetic acid, crotylidene-, Crotylidene acetic acid, Crotylidene-Acetic acid, foodpreservative-sorbicacidpurity, Hexa-2,4-dienoic acid, Hexa-2,4-dienoic acid, (E,E)-, Hexadienic acid, Hexadienoic acid, Hexadienoic acid, (E,E), Hexadienoic acid1,3-pentadiene-1-carboxylic acid, Kyselina 1,3-pentadien-1-karboxylova [Czech], Kyselina sorbova [Czech], Panosorb, Parasorbic Acid, Preservastat, Sorbic Acid, (E,E)- [USAN], sorbic acid-分析标准品 [Chinese], Sorbins??ure, Sorbinsaeure, Sorbistat [Trade name], UNII-X045WJ989B, α-trans-Laquo γRaquo -trans-sorbic acid, α-trans-γ-trans-Sorbic acid, 山梨酸 [Chinese]

E 200 was first isolated from the unripe berries of the Sorbus aucuparia (rowan tree), hence its name.
The traditional route to E 200 involves condensation of malonic acid and crotonaldehyde.
E 200 can also be prepared from isomeric hexadienoic acids, which are available via a nickel-catalyzed reaction of allyl chloride, acetylene, and carbon monoxide.
The route used commercially, however, is from crotonaldehyde and ketene.
An estimated 30,000 tons are produced annually.

History of E 200
E 200 was isolated in 1859 by distillation of rowanberry oil by A. W. von Hofmann.
This affords parasorbic acid, the lactone of E 200 , which he converted to sorbic acid by hydrolysis.
Its antimicrobial activities were discovered in the late 1930s and 1940s, and it became commercially available in the late 1940s and 1950s.
Beginning in the 1980s,E 200 and its salts were used as inhibitors of Clostridium botulinum in meat products to replace the use of nitrites, which can produce carcinogenic nitrosamines.

Properties and uses of E 200
With a pKa of 4.76, E 200 is about as acidic as acetic acid.
E 200 and its salts, especially potassium sorbate and calcium sorbate, are antimicrobial agents often used as preservatives in food and drinks to prevent the growth of mold, yeast, and fungi.
In general the salts are preferred over the acid form because they are more soluble in water, but the active form is the acid.
The optimal pH for the antimicrobial activity is below pH 6.5.

Sorbates are generally used at concentrations of 0.025% to 0.10%.
Adding sorbate salts to food will, however, raise the pH of the food slightly so the pH may need to be adjusted to assure safety.
E 200 is found in foods such as various kinds of cheese, bread, muffins, donuts, pies, cookies, protein bars, syrups, lemonades, fruit juices, dried meats, sausages, nuggets, burgers, sandwiches, tacos, pizzas, smoked fish, margarine, sauces, soups, and more.

E 200 appears as white powder or crystals.
Slightly acidic and astringent taste with a faint odor.
Molar mass: 112.128 g·mol−1
Density: 1.204 g/cm3
Melting point: 135 °C
Boiling point: 228 °C

E 200 is a hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.
E 200 is a hexadienoic acid, a polyunsaturated fatty acid, a medium-chain fatty acid and an alpha,beta-unsaturated monocarboxylic acid.
E 200 is a conjugate acid of a sorbate.
E 200 is a natural product found in Prunus domestica and Schisandra chinensis with data available.

E 200 is a naturally occurring compound that’s become the most commonly used food preservative in the world, and it makes the global food chain possible.
E 200’s highly effective at inhibiting the growth of mold, which can spoil food and spread fatal diseases.
For example, when E 200 is sprayed on the exterior of a country ham, there won’t be any mold growth for 30 days.
This allows for food to be shipped and stored all over the globe.

E 200 is a preferred preservative compared to nitrates, which can form carcinogenic byproducts.
E 200’s applied to food by either spraying or dipping the food with a solution of sorbic acid and water.
Sorbic acid is most commonly found in foods, animal feeds, pharmaceutical drugs, and cosmetics.

When it comes to human foods, E 200 is most commonly used in:
wines
cheeses
baked goods
fresh produce
refrigerated meat and shellfish

E 200 is used to preserve meats because of its natural antibiotic capabilities.
In fact, its earliest use was against one of the deadliest toxins known to mankind, the bacteria Clostridium botulinum, which can cause botulism.
Its use saved countless lives by preventing bacterial growth while allowing meats to be transported and stored safely.
Because of its anti-fungal properties, E 200 is also used in canned goods, including pickles, prunes, maraschino cherries, figs, and prepared salads.
E 200 and its potassium salt are widely used antimicrobial preservatives in foods, especially for preventing mold growth on food products.

E 200 is a versatile and safe food preservative that is highly effective against bacteria, molds and yeasts.
E 200 is included in the food additive lists with the code E200.
E 200 is widely used as a food preservative due to its antimicrobial properties.
The amount allowed for E 200 use in foods is about 0.5% to 0.025%.
E 200 is used very effectively against a large number of micro-organisms.

For the first time, I see E 200 obtained from the ripe fruit of the bird ash (Sorbus aucuparia) tree, it is called by this name.
Anti-pressure and antimycotic effects of acid were used in 1945.
With this development, E 200 is given as a preservative in the provision of food.
Sodium sorbate, calcium sorbate, potassium sorbate are E 200 salts that deplete mold and yeast products.
Since they have the properties of these different files, their application areas are extremely wide.

E 200 has a white color, a unique and non-pungent odor.
E 200 is an unsaturated fatty acid in powder or granular form, free from dust with free exhaust.
While E 200 is slightly soluble in water, it dissolves better in oil.
In alcohol, E 200 is completely soluble.
The most suitable pH value in E 200 is 6.5.
E 200 is widely used in food inspection.
E 200 is especially used to prolong shelf life and prevent micro-growth such as cheese, yoghurt, rye bread, pizza, pasta, meat products, carbonated drinks, fruit juices, distributed fruits, instant soups, cabbage and pickled cucumbers.
The effect on mold and yeast formation is higher than the effect on materials.

Usage areas of E 200
The use of E 200 can be during the production of foods, or E 200 can be used by spraying on foods after production.
E 200 is added to foods in dissolved or dry form depending on the use.
However, E 200 is appropriate to add it to foods that will be heat treated for a long time, after heat treatment.
E 200 can also be used in personal care products, pharmaceuticals, cosmetics and some industrial products.
Determination of the ratio of E 200 to be added to foods is made depending on the humidity, temperature, pH value of the environment and the way of packaging.
If these ratios are correct, the taste and smell of the food will not change.
Although there are no side effects, sometimes allergic reactions can occur.

E 200 and potassium sorbate are used to effectively manage mold and yeast in the production of:
cheese,
baked goods,
fruit juices,
fresh fruits and vegetables,
wines,
soft drinks,
pickles,
sauerkraut, and
some fish and meat items.

First Aid of E 200
EYES:
First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN:
IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop.
IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.

INHALATION:
IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION:
DO NOT INDUCE VOMITING.
Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.

IMMEDIATELY transport the victim to a hospital.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.
DO NOT INDUCE VOMITING.
Transport the victim IMMEDIATELY to a hospital.

Hazard classification & labelling of E 200
Warning! According to the classification provided by companies to ECHA in REACH registrations E 200 causes serious eye irritation and causes skin irritation.

About E 200
E 200 is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
E 200 is used by consumers, in formulation or re-packing, at industrial sites and in manufacturing.

Biocidal Uses of E 200
E 200 is being reviewed for use as a biocide in the EEA and/or Switzerland, for: product preservation.

Consumer Uses of E 200
E 200 is used in the following products: cosmetics and personal care products.
Other release to the environment of E 200 is likely to occur from: indoor use as processing aid.

Formulation
Release to the environment of E 200 can occur from industrial use: formulation of mixtures.

Uses at industry
E 200 is used in the following products: polymers.
E 200 is used for the manufacture of: plastic products and rubber products.
Release to the environment of E 200 can occur from industrial use: as processing aid and as processing aid.

Manufacture of E 200
Release to the environment of E 200 can occur from industrial use: manufacturing of the substance.